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New Chiral Borohydrides. 2. Preparation of Potassium B-Methoxydiisopinocampheylborohydride and Its Asymmetric Reducing Properties
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  • New Chiral Borohydrides. 2. Preparation of Potassium B-Methoxydiisopinocampheylborohydride and Its Asymmetric Reducing Properties
  • New Chiral Borohydrides. 2. Preparation of Potassium B-Methoxydiisopinocampheylborohydride and Its Asymmetric Reducing Properties
저자명
Cho. Byung-Tae
간행물명
Bulletin of the Korean Chemical Society
권/호정보
1991년|12권 6호|pp.662-665 (4 pages)
발행정보
대한화학회
파일정보
정기간행물|ENG|
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이 논문은 한국과학기술정보연구원과 논문 연계를 통해 무료로 제공되는 원문입니다.
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기타언어초록

In order to prepare new chiral borohydrides (4) possessing chirality on dialkyl moieties, a series of B-alkoxydiisopinocampheylborinates (3) were synthesized by treatment of diisopinocampheylborane ($Ipc_2BH$) with alcohols (R in ROH: Me, Et, i-Pr, t-Bu) and reacted with excess of potassium hydride. Of these chiral borinic esters, only B-methoxydiisopinocampheyl borinate (3a) was converted into the corresponding dialkylmonoalkoxyborohydride (4a). For the other borinic esters, hydride uptake reactions were very slow at room temperature, accompanying disproportionation products at $65^{circ}C$. The hydride (4a) formed is stable at $0^{circ}C$ and can be stored over potassium hydride for few months. In the asymmetric reduction of the selected ketones, 4a provided the corresponding alcohols, such as 21% ee for 3-methyl-2-butanone, 11% ee for 2,2-dimethylcyclopentanone, 24% ee for acetophenone, 32% ee for 3-acetylpyridine, 30% for methyl benzoylformate, 31% ee for 4-phenyl-3-butyn-2-one, 39% ee for 3-butyn-2-one, and 34% ee for 3-hexyn-2-one.